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A Hybrid P,N-Ligand Functionalized Imidazolium Salt for Palladium-Catalyzed Heck Reactions in Ionic Liquid Solution

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Abstract

A hybrid P,N-donor functionalized imidazolium salt has been synthesized and investigated as a ligand for the palladium catalyzed Heck reaction. Due to the advantageous features of this hybrid P,N-donor like the hemilabile ligation to Pd center, the improved oxidation tolerance and the ionophilicity, the derived palladium catalyst served as an efficient, stable and recyclable system even after seven reuses.

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References

  1. Shibasaki M, Vogl EM, Ohshima T (2004) Adv Synth Catal 346:1533

    Article  CAS  Google Scholar 

  2. Bedford RB, Cazin CSJ, Holder D (2004) Coord Chem Rev 248:2283

    Article  CAS  Google Scholar 

  3. Nicolaou KC, Bulger PG, Sarlah D (2005) Angew Chem Int Ed Engl 44:4442

    Article  CAS  Google Scholar 

  4. Amatore C, Jutand A (2000) Acc Chem Res 33:314

    Article  CAS  Google Scholar 

  5. Consorti CS, Flores FR, Dupont J (2005) J Am Chem Soc 127:12054

    Article  CAS  Google Scholar 

  6. Beletskaya IP, Cheprakov AV (2004) J Organomet Chem 689:4055

    Article  CAS  Google Scholar 

  7. Prökl SS, Kleist W, Gruber MA, Köhler K (2004) Angew Chem Int Ed 43:1881

    Article  Google Scholar 

  8. Calo V, Nacci A, Monopoli A, Lopez L, Cosmo A (2001) Tetrahedron 57:6071

    Article  CAS  Google Scholar 

  9. Bergbreiter DE, Osburn PL, Wilson A, Sink E (2000) J Am Chem Soc 122:9058

    Article  CAS  Google Scholar 

  10. Zapf A, Beller M (2005) Chem Commun 431 (and references cited therein)

  11. Kuhl O (2007) Chem Soc Rev 36:592

    Article  Google Scholar 

  12. Sommer WJ, Weck M (2007) Coordin Chem Rev 251:860

    Article  CAS  Google Scholar 

  13. Ozdemir I, Demir S, Cetinkaya B (2007) Synlett 6:889

    Article  Google Scholar 

  14. Peris E, Crabtree RH (2004) Coordin Chem Rev 248:2239

    Article  CAS  Google Scholar 

  15. Viciu MS, Nolan SP (2005) Top Organomet Chem 14:241

    CAS  Google Scholar 

  16. Cui X, Zhou Y, Wang N, Liu L, Guo QX (2007) Tetrahedron Lett 48:163

    Article  CAS  Google Scholar 

  17. Migowski P, Dupont J (2007) Chem Eur J 13:32

    Article  Google Scholar 

  18. Li S, Lin Y, Xie H, Zhang S, Xu J (2006) Org Lett 8:391

    Article  CAS  Google Scholar 

  19. Cui X, Tao C, Xu Y, Liu L, Guo Q (2006) Org Lett 8:2467

    Article  CAS  Google Scholar 

  20. Beford RB (2003) Chem Commun 1787

  21. Mo J, Xu L, Xiao J (2005) J Am Chem Soc 127:751

    Article  CAS  Google Scholar 

  22. Cabri W, Candiani I (1995) Acc Chem Res 28:2

    Article  CAS  Google Scholar 

  23. Shaw BL, Perera SD (1998) Chem Commun 1863. Pathak DD, Maheswaran H

  24. Prasanth KL, Kantam ML (2007) Synlett 5:757

    Google Scholar 

  25. Nilsson P, Larhed M, Hallberg A (2003) J Am Chem Soc 125:3430

    Article  CAS  Google Scholar 

  26. Nilsson P, Larhed M, Hallberg A (2001) J Am Chem Soc 123:8217

    Article  CAS  Google Scholar 

  27. Arndt H-D (2006) Angew Chem Int Ed 45:4152

    Article  Google Scholar 

  28. Braunstein P, Naud F (2001) Angew Chem Int Ed 40:680

    Article  CAS  Google Scholar 

  29. Reddy KR, Surekha K, Lee G-H, Peng S-M, Liu S-T (2000) Organometallics 19:2637

    Article  CAS  Google Scholar 

  30. Espinet P, Soulantica K (1999) Coordin Chem Rev 193–195:499

    Article  Google Scholar 

  31. Zotto AD, Zangrando E, Baratta W, Felluga A, Martinuzzi P, Rigo P (2005) Eur J Inorg Chem 4707

  32. Zhang Z-Z, Cheng H (1996) Coord Chem Rev 147:1

    Article  CAS  Google Scholar 

  33. Lindner E, Pautz S, Haustein M (1996) Coord Chem Rev 155:145

    Article  CAS  Google Scholar 

  34. Slone CS, Weinberger DA, Mirkin CA (1999) Progr Inorg Chem 48:233

    Article  CAS  Google Scholar 

  35. Reetz MT, Demuth R, Goddard R (1998) Tetrahedron Lett 39:7089

    Article  CAS  Google Scholar 

  36. Schultz T, Schmees N, Pfaltz A (2004) Mater Nanosci Catal 18:595

    CAS  Google Scholar 

  37. Sun Y, Thiel WR (2006) Inorg Chim Acta 359:4807

    Article  CAS  Google Scholar 

  38. Smiglak M, Metlen A, Rogers RD (2007) Acc Chem Res 40:1182

    Article  CAS  Google Scholar 

  39. Cai YQ, Lu Y, Liu Y, Gao GH (2007) Catal Lett 119:154

    Article  CAS  Google Scholar 

  40. Dubbaka SR, Zhao DB, Fei ZF, Volla CMR, Dyson PJ, Vogel P (2006) Synlett 3155

  41. Jain N, Kumar A, Chauhan S, Chouhan SMS (2005) Tetrahedron 61:1015

    Article  CAS  Google Scholar 

  42. MacFarlane DR, Pringle JM, Johansson KM, Forsyth SA, Forsyth M (2006) Chem Commun 1905

  43. Wilkes JS (2002) Green Chem 4:73

    Article  CAS  Google Scholar 

  44. Wan Q, Liu Y, Li M, Lu Y, Wu H (2008) Catal Lett 121:331

    Article  CAS  Google Scholar 

  45. Sirieix J, Ossberger M, Betzemeier B, Knochel P (2000) Synlett 11:1613

    Google Scholar 

  46. Xu L, Chen W, Xiao J (2000) Organometallics 19:1123

    Article  CAS  Google Scholar 

  47. Mathews CJ, Smith PJ, Welton T, White AJP, Williams DJ (2001) Organometallics 20:3848

    Article  CAS  Google Scholar 

  48. Yang C, Lee HM, Nolan SP (2001) Org Lett 3:1511

    Article  CAS  Google Scholar 

  49. Kwong FY, Klapars A, Buchwald SL (2002) Org Lett 4:581

    Article  CAS  Google Scholar 

  50. Wang R, Twamley B, Shreeve JM (2006) J Org Chem 71:426

    Article  CAS  Google Scholar 

  51. Ecke A, Kein W, Bonnet MC, Tkatchenko I, Dahan F (1995) Organometallics 14:5302

    Article  CAS  Google Scholar 

  52. Drent E, Arnoldy P, Budzelaar PHM (1994) J Organomet Chem 475:57

    Article  CAS  Google Scholar 

  53. Drent E, Arnoldy P, Budzelaar PHM (1993) J Organomet Chem 455:247

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The National Natural Science Foundation of China (No. 20533010, No. 20590366, No. 20673039), the Science & Technology Commission of Shanghai Municipality (No. 06JC14023, 06SR07101), and Shanghai Leading Academic Discipline Project (B409) are gratefully acknowledged for financial support.

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Authors and Affiliations

  1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai, 200062, China

    Qing-Xia Wan, Ye Liu & Yue-Qin Cai

Authors
  1. Qing-Xia Wan
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  2. Ye Liu
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  3. Yue-Qin Cai
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Correspondence to Ye Liu.

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Wan, QX., Liu, Y. & Cai, YQ. A Hybrid P,N-Ligand Functionalized Imidazolium Salt for Palladium-Catalyzed Heck Reactions in Ionic Liquid Solution. Catal Lett 127, 386–391 (2009). https://doi.org/10.1007/s10562-008-9700-5

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